Winter Park Homes with HOA Yes/No

Winter Park Homes with HOA Yes/No

Winter Park, located in Orange County, Florida, is a charming city that offers a wonderful place to call home. With its picturesque streets, lush greenery, and vibrant community, Winter Park is a highly sought-after region for real estate.

One of the key aspects to consider when looking for homes in Winter Park is the presence of Homeowners Association (HOA) communities. In this region, you will find a mix of homes with HOA and homes without HOA.

For those seeking the benefits of living in an HOA community, Winter Park has plenty to offer. HOA communities often provide amenities such as swimming pools, fitness centers, parks, and community events. These communities also have rules and regulations in place to maintain the appearance and value of the properties, ensuring a well-kept neighborhood.

On the other hand, if you prefer more flexibility and freedom in how you use and maintain your property, there are also homes available in Winter Park without HOA. These properties give homeowners the autonomy to make decisions about their home and land without the restrictions of an HOA.

Whether you choose a home with or without an HOA, Winter Park has a wide range of housing options to suit different preferences and budgets. From cozy single-family homes to spacious townhouses and luxurious estates, there is something for everyone in this vibrant region.

With its beautiful surroundings, convenient location, and diverse real estate options, Winter Park is truly a place where you can find your dream home.

Newest Winter Park Homes with HOA Yes/No

$180,000
1 Beds ⋅ 1 Baths ⋅ Waterfall Cove At Winter Park Condominium D107 SubDv. ⋅ 32789 Zip Code
Don't miss out the great opportunity to own a unit in the heart of Winter Park Area. A perfect primary or secondary residence or investment home. Waterfall Cove is a great community with spacious pool, playground and lots of lush landscaping. Easy access to Major Highways a minute from I-4, bike away from Downtown Winter Park, close to major theme parks, major shopping area, restaurant, movie theater and a short drive to Cocoa Beach.

1695 Lee Road Unit D107, Winter Park
$1,000,050
4 Beds ⋅ 3 Baths ⋅ Park Pointe Rep SubDv. ⋅ 32789 Zip Code
A MUST SEE BEAUTIFUL WELL MAINTAINED POOL HOME by ORIGINAL OWNERS in SOUGHT AFTER WINTER PARK ZIPCODE & SCHOOLS. PICTURES PROVIDE a GREAT PORTRAYAL of the FLOORPLAN but THERE ARE MANY FEATURES TO POINT OUT - THIS 2868 SQFT HOME has a 3-WAY SPLIT with 4 BEDROOMS, 3 FULL BATHROOMS, plus BONUS ROOM & OFFICE. YOU WILL NOT BELIEVE ALL THE STORAGE, STORAGE, STORAGE UNDER AIR! The BONUS ROOM (12.4 X 11.7) OFF PRIMARY BEDROOM COULD BE a NURSERY, OFFICE, EXERCISE ROOM, or OWNERS RETREAT. There is an ADDITIONAL OFFICE (13.6 X 11.6 ) with BUILT N DESK & STORAGE CABINETS MAKING a GREAT HOMESCHOOL ROOM, CRAFT AREA, or HOME OFFICE WHERE a PRIVATE EXTERIOR ENTRY DOOR is NEEDED. ONE BEDROOM could be USED as an IN-LAW SUITE with IT’S ENSUITE BATHROOM with SHOWER. The SPACIOUS GARAGE has NEW SHARK FLOORING (7/26), NEW PAINT, NEW ELECTRIC CAR CHARGING OUTLET (6/26), NEW INSULATED GARAGE DOOR & A MINI SPLIT AC – LOTS OF POSSIBILITIES! MANY FUN MEMORIES can be ENJOYED with FAMILY & FRIENDS AROUND the BEAUTIFUL SCREENED POOL & LARGE COVERED LANAI & DECK ( RESURFACED 9/25 ) The NEW OWNER of this LOVELY HOME will APPRECIATE all the UPDATES that have BEEN DONE over LAST FEW YEARS – NEW $29K LENOX UPGRADED AC (3/26), NEW FRONT DOOR (4/26), NEW GOOGLE NEST DOORBELL (3/26), NEW INSULATION in ATTIC & ON GARAGE DOOR (6/26), NEW PAVER DRIVEWAY (5/26 ) NEW UPGRADED FLASHING AROUND CHIMNEY (5/26), GAS TANKLESS WATER HEATER W RECIRCULATING FEATURE(2023), NEW DUCT WORK (2019) NEW WINDOWS (2020), WHOLE HOUSE REPLUMBED (2020), ROOF (2016), STAINLESS APPLIANCES (2019), WHOLE HOUSE WATER SOFTNER & DOUBLE OSMOSIS SYSTEM for DRINKING WATER, SELLER WILL CONSIDER CARPET ALLOWANCE WITH ACCEPTABLE OFFER. ****** THIS HOME IS WORTH SEEING ******

2667 Cochise Trail, Winter Park
$510,000
3 Beds ⋅ 3 Baths ⋅ Villas Of Aragon Condo SubDv. ⋅ 32789 Zip Code
Excellent Winter Park location! This 3 bedroom 2.5 bath quad-condo LIVES LIKE A PRIVATE 2-STORY HOME, with attached oversized 2 car garage, private patio and back fenced area. (The unit is attached to another only by a common garage wall.) Priced below market value to be sold AS-IS for the seller's convenience and TLC needed. ** One Year AHS Home Warranty included.** Nestled between Denning Dr and Orlando Ave, this home is an easy walk to the vibrant charm of Park Avenue, and close to the Winter Park Library, SunRail, and Rollins College. Publix and restaurants are just down the street! The first floor is tiled, with foyer entry, and comfortable family/dining/kitchen living area complete with fireplace. Sliding doors lead to a private patio. Upstairs, the large primary suite is a nice retreat with high ceilings, double walk in closets, double vanity and ample sized shower. Two more bedrooms and another bath complete the 2nd floor. High end washer and dryer are included in the attached garage, and a full wall workshop is in the garage too. Call to see it today!

1061 Aragon Avenue Unit 1061, Winter Park
$3,895,000
3 Beds ⋅ 5 Baths ⋅ South Interlachen Place SubDv. ⋅ 32789 Zip Code
From the moment you enter this custom residence you feel welcomed home by the understated elegance and gracious living spaces. SE corner location affording abundant natural light. From the underground private two car garage through the three living levels and up to the roof top terrace, each floor is serviced by a window wrapped staircase and your own private elevator. Creature comforts include a Lutron lighting system, home audio system and programmable shades, all set to your schedule by the Control4 home automation system. You approach the double entry doors via a gated, spacious terrace. The main level offers spacious living and dining areas opening to a Chef’s Dream Kitchen. Here you find solid wood cabinetry, quartz countertops, custom backsplash, Wolf five-burner natural gas cooktop, integrated Sub Zero refrigerator, Wolf wall oven and microwave, Bosch dishwasher, Sub Zero full size, dual zone wine refrigerator and a large island with counter seating. The adjacent sitting room faces East for starting your day with morning light or winding down your day with your favorite beverage. The wall mounted television adds to the convenience of this versatile space where you can catch up on the morning or evening news. The main living level also offers your guests the convenience of a private powder room. The second level is dedicated to the generous Primary Suite. This level offers a spacious bedroom, a custom walk-in closet, a gracious primary bathroom with a walk-in shower, double sinks, a custom vanity/makeup area, and a private water closet with automatic Toto Washlet. The Primary Suite level also features a customized office/lounge area with built-in cabinetry and a refrigerator. Adding to the convenience, you’ll find the laundry area integrated into the Primary Suite level. You are greeted to the Third Level through an open media room. The media loft area is adjacent to the two spacious and private ensuite bedrooms. Both bedrooms 2 and 3 feature walk-in closets and private bathrooms. Wait, there’s more! Up one more level you will find the incredible rooftop terrace. This approx. 800 sq. ft. space, serviced by your private elevator, is perfect for entertaining family and friends – no matter the size of the party! An entertainer’s delight, you will enjoy the outdoor kitchen with stainless 36” DCS natural gas grill, exhaust hood, refrigerator and sink. Adding to the convenience of entertaining on your private rooftop, this terrace has its own powder room. Additionally, there is an air-conditioned storage closet perfect for keeping dry and safe items you want protected from the weather. Going back downstairs to the underground garage, you’ll enjoy the security of your own oversized two-car garage. Not only does this level of Residence #1 offer you a private garage, you’ll also love the convenience and security of your own air-conditioned 9x13 storage room and another private foyer. The building’s garage area is accessed through a separate gated entrance. This underground parking area includes guest parking spaces. This exquisite residence is mere steps from all the dining, shopping and community amenities along Park Avenue and the adjacent Boulevards that make downtown Winter Park so coveted. Residence 1 of 125 South Interlachen Place is that rare opportunity to own an exquisite and perfectly located home offering the lock and leave lifestyle. All measurements are approximate and Buyer is responsible for verifying all dimensions.

125 S Interlachen Avenue Unit 1, Winter Park
$719,900
4 Beds ⋅ 4 Baths ⋅ Swoope Park SubDv. ⋅ 32789 Zip Code
Virtually Staged. Welcome to this virtually staged contemporary townhome in the desirable 400 West community, home to just nine residences and steps away from lively Park Avenue. Enter through the private garage or the charming front path, and you'll find a bright and open main floor that perfectly balances comfort and modern style. The main floor features a stylish mix of finishes, including large-format porcelain tiles, level 4 drywall, tall baseboards, and designer lighting. The centerpiece is a sleek kitchen equipped with glossy white cabinetry, chic chrome pulls, quartz countertops, and top-quality stainless-steel appliances. The garage, with alley access, includes a storage closet and built-in shelving for added convenience. On the second level, discover two spacious primary suites with modern LVP flooring and large windows that let in plenty of natural light. The en-suite bathrooms are designed with porcelain tiles, frameless glass showers, wall-to-wall mirrors, and matte white vanities. The primary bath offers a double-sink vanity, a private water closet, and a spacious walk-in closet. A conveniently situated laundry room features a Samsung washer and dryer with overhead storage. The third level has two more bedrooms, each with walk-in closets, connected by a shared Jack-and-Jill bath, making it ideal for guests, a home office, or a workout space. Don’t miss the chance to check out this fantastic home in a prime location where luxury meets practicality!

436 W Swoope Avenue, Winter Park
$88,999
1 Beds ⋅ 1 Baths ⋅ Waterfall Cove Of Winter Park SubDv. ⋅ 32789 Zip Code
This charming 1bedroom, 1bathroom condo is a fantastic opportunity for both homeowners and investors. Located in a desirable area close to shopping, restaurants, and everyday conveniences, it offers comfort, convenience, and excellent value. The kitchen comes fully equipped with a refrigerator, stove, dishwasher, and microwave, and the unit also includes a washer and dryer for added convenience. Step outside onto your private outdoor balcony, the perfect spot to enjoy your morning coffee or unwind after a long day. Residents have access to a beautiful community swimming pool, creating a relaxing atmosphere to enjoy year-round. Whether you're looking for a place to call home or a great investment property, this condo has everything you need in an ideal location.

1695 Lee Road Unit B108, Winter Park
$190,000
1 Beds ⋅ 1 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code
Welcome to this beautifully updated one-bedroom, one-bath condo in the heart of Winter Park. Thoughtfully maintained and move-in ready, this inviting home offers a bright, clean interior with tasteful finishes and a functional layout designed for comfortable, low-maintenance living. A spacious screened porch overlooks a serene courtyard, creating the perfect spot to enjoy your morning coffee or unwind at the end of the day. Perfectly situated, this home is nestled between two beautiful parks—Mead Botanical Garden, just steps away, and Seven Oaks Park—offering easy access to nature, walking paths, and green space. You're also just minutes from Rollins College, the boutiques and restaurants of Park Avenue, AdventHealth Winter Park, and the vibrant Mills 50 District. Outdoor enthusiasts will appreciate the nearby Cady Way Trail, Orlando Urban Trail, Dinky Line Trail, and Baldwin Park, all just a short bike ride away. With convenient access to Orlando Avenue (US-17/92), I-4, and both the Winter Park and AdventHealth SunRail stations, commuting throughout Central Florida is effortless. Located in the desirable Mead Garden Condominiums community with a sparkling pool and beautifully maintained grounds, this charming condo offers an exceptional blend of comfort, convenience, and the best of the Winter Park lifestyle.

1250 S Denning Drive Unit 109, Winter Park
$1,025,000
3 Beds ⋅ 3 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code
Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

1138 S Pennsylvania Avenue, Winter Park
$2,800,000
3 Beds ⋅ 4 Baths ⋅ Morse & Pennsylvania Twnhms SubDv. ⋅ 32789 Zip Code
Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desirable locations. Situated in the heart of Hannibal Square and just three blocks from Park Avenue, this residence places premier dining, shopping, galleries, museums, Central Park and year-round community events within easy walking distance. Thoughtfully designed with both style and functionality in mind, the home showcases high-end finishes throughout including rich Brazilian walnut flooring, oversized 24 x 48 ceramic tile, coffered ceilings, quartz countertops, custom cabinetry and premium stainless-steel appliances. The chef’s kitchen is anchored by an eight-burner Wolf gas range and a Sub-Zero refrigerator, paired with a hidden pantry discreetly concealed behind custom cabinetry. A striking metal staircase serves as a central architectural feature, adding a contemporary design element that complements the home’s clean lines and sophisticated aesthetic. The open-concept floor plan is filled with natural light, enhanced by expansive windows throughout that frame peaceful green views and mature tree-lined surroundings. The main living areas extend seamlessly to the outdoors, where a first-floor entertaining wet bar with a wine refrigerator opens directly to the private courtyard, creating an effortless indoor-outdoor flow ideal for hosting. The courtyard features a fire pit surrounded by greenery, while the balcony off the main living area includes a summer kitchen. A fenced yard offers privacy and space for pets to enjoy. Designed for today’s lifestyle, the home includes a PRIVATE ELEVATOR servicing all three floors, dual HVAC systems, two tankless water heaters hardwired security cameras and a spacious three-car garage with an electric vehicle charging station and generous storage space. RARELY AVAILABLE in Downtown Winter Park, the oversized THREE CAR GARAGE offers exceptional functionality and flexibility. The private driveway provides additional parking while abundant guest parking nearby makes entertaining easy, an uncommon convenience in a downtown setting. The primary suite occupies the third floor, offering a private retreat with separation from the main living areas. It features a very large owner’s closet filled with natural light and a dedicated vanity area, creating a functional yet refined dressing space. Two additional bedrooms and a dedicated office or den provide flexibility for working from home, accommodating guests or creating additional living space. Each bathroom has been thoughtfully appointed with quality finishes and timeless design. Tucked within a quiet enclave , this residence offers a unique balance of privacy and walkability. The property is adjacent to the recently completed $6.1 million residence of internationally respected architect Kamal Rizk further underscoring the caliber of the surrounding neighborhood. Homes of this quality and location rarely come to market, presenting a truly limited opportunity to own in one of Winter Park’s most sought-after addresses. Combining the architectural vision and craftsmanship of Phil Kean Design Group with luxury finishes, modern conveniences and an exceptional location, this residence offers sophisticated low-maintenance living in the heart of Winter Park’s most vibrant neighborhood. Furniture may convey and pricing upon request. New 10 yr. termite bond will convey with the sale.

660 W Morse Boulevard, Winter Park
$449,000
32789 Zip Code
Some opportunities don't announce themselves. They show up quietly in Winter Park's most sought-after zip code, waiting for someone who knows exactly what to do with them. This vacant lot inside Waterbridge sits in the 32789 zip code, a rare chance to build the home you've always had in mind, in a neighborhood that has already decided who it is. Waterbridge is a tight-knit, tree-lined enclave where the homes are custom and the neighbors stay. Lots like this do not come available often. The address puts you minutes from Park Avenue's galleries and weekend farmers market, AdventHealth Winter Park, and the employers and services that make this corridor one of Winter Park's most connected. The schools zoned here, Glenridge Middle and Winter Park High, are among the most respected in Orange County and part of why buyers seek out this zip code specifically. Build the primary suite you've never been able to find. Design the kitchen around how you actually cook. Choose the ceiling heights, the materials, the layout. Every decision a resale home will never let you make is yours to make here. A lot in Waterbridge represents something that rarely surfaces: the convergence of a blank canvas and a proven address.

Jessica Court, Winter Park
$899,000
3 Beds ⋅ 4 Baths ⋅ H Vanwies Sub SubDv. ⋅ 32789 Zip Code
Built in 2023 by SGC Homes, this exceptionally livable modern Mediterranean townhome blends comfort and convenience in a classic architectural package, offering 3 bedrooms, 3-1/2 baths, and no shared internal walls, for perfect privacy. There is so much to love here. Situated on a tree-lined brick street in the walkable, convenient area of Minnesota Row, this beauty has been lightly occupied as a second home, and it has never been rented. It is truly a blank slate to make your own. Features that make it special include an open yet cozy floor plan, with a roomy ground floor primary suite which includes a walk-in closet, designer bath with 2 sinks, soaking tub and separate shower, as well as Electrolux washer and dryer, for main-floor convenience. The chef's kitchen with high-end appliances looks into the combined living and dining space. Direct access from the 2-car garage into the kitchen and a very private garden complete the ground floor. Upstairs you'll find two bedrooms, both en suite, separated by an open sitting area for a little extra living space, and a second floor larger laundry with a sink and cabinets for additional storage. Large windows make the rooms light and bright, and the house is ideally situated for maximum privacy. You're going to love the finishes in this unit, including the engineered wood floors, fans in all bedrooms and high end light fixtures, as well tankless hot water, and pavers on the outdoor areas. Easy access to all the options in charming Winter Park including Park Avenue, Winter Park Village, Rollins College and the many parks and green spaces, as well as more shops and dining in College Park. I-4 is minutes away, to get to any place in and around Orlando.

1411 Miller Avenue, Winter Park
$244,900
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
New Price/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and laminate for easy care...no carpet. Enjoy the dining space that opens to the large great room and balcony where you'll love sitting in the evenings to relax. SPACIOUS BEDROOMS - Primary bedroom has an attached full bathroom and bedroom 2 has a LARGE walk-in closet. The 2nd Full Bathroom is accessed via a common hallway. The Chateaux Du Luc LAKEFRONT COMMUNITY offers FABULOUS AMENITIES that include an oversized heated pool, clubhouse, community deck, BBQ grill, 2 on-site saunas, updated on-site laundry facilities, and a resident-only boat ramp on skiable Lake Killarney. There's even storage for your Kayak or paddleboard! Roof 2025. Reach out today for your personal showing!!

1500 Gay Road Unit 3C, Winter Park
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