Winter Park Homes with Deed Restrictions Community Features

Winter Park Homes with Deed Restrictions Community Features

Welcome to Winter Park, Florida—a picturesque city renowned for its charming tree-lined streets, vibrant cultural scene, and a welcoming community spirit. Nestled just north of Orlando, Winter Park offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place to call home. With its stunning lakes, lush parks, and beautiful gardens, the city is a haven for outdoor enthusiasts and those who appreciate nature’s beauty.

One of the standout features of Winter Park is its array of homes nestled within deed-restricted communities. These neighborhoods are designed to uphold a high standard of living, ensuring that properties maintain their aesthetic appeal and value over time. Residents can enjoy the peace of mind that comes with knowing their community is well-maintained and governed by established guidelines. From beautifully landscaped front yards to meticulously maintained common areas, these homes reflect a commitment to quality and community pride.

Living in a deed-restricted community in Winter Park means access to a host of amenities, including community pools, recreational facilities, and walking trails. These neighborhoods often foster a strong sense of camaraderie among residents, with organized events and activities that encourage social interaction and community engagement.

Whether you’re seeking a cozy bungalow or an elegant estate, Winter Park’s deed-restricted communities offer a diverse range of options that cater to various lifestyles. Embrace the charm of Winter Park and discover a place where you can truly feel at home!

Newest Winter Park Homes with Deed Restrictions Community Features

$249,900
2 Beds ⋅ 3 Baths ⋅ Whisperwood Condo SubDv. ⋅ 32792 Zip Code
OWNER FINANCE may be available with down payment. Unique 4 Bedroom 3 bath unit. Perfect for investors looking to rent to college attendees at UCF and surrounding or for larger families needing 4th bedroom. Lots of upgrades including 2 new bathrooms, new laundry room, new flooring and lots of new paint. Brand new AC system installed in 2025 and hot water heater in 2022. Granite counters, stainless appliances, ceiling fans and tons of storage. Rear screened and covered lanai off living room, covered and open rear private yard/ garden off kitchen and private balcony off master bedroom. Minutes to UCF, lots of shopping and all major highways

7487 Canford Court Unit 5, Winter Park
$230,000
2 Beds ⋅ 2 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code
WHAT A GEM! Tucked away in a private, sought after community and so conveniently located in breathtaking Winter Park. Here’s a beautifully maintained, upgraded and move-in ready home. With 2 large bedrooms and 1.5 bathrooms, this unit spans 1,219 square feet, providing an ideal space for cozy living. Enjoy the benefits of a peaceful and friendly community, with well-manicured grounds and a welcoming atmosphere. This charming home has been tastefully updated with upgraded laminate flooring, a renovated kitchen with granite countertops, newer cabinets and a stylish backsplash. The floor plan offers a dining & family room open combination which looks out on the porch and brings in plenty of natural light. Both nicely sized bedroom suites are on the second floor and have a shared & updated bathroom. Ample storage on the back patio for your bike and all your extra toys allowing you to enjoy your weekends. This is an extremely well managed community with an onsite manager taking pride in the community and care for their residents. Four Seasons community provides super amenities including a cubhouse with library, a renovated fitness center, 3 swimming pools, tennis courts, a laundry facility steps away and shuffleboard. Walk to Cady Way Park with tennis courts, baseball and soccer fields, playgrounds, community pool and Cady Way Trail. Minutes to Advent Health Winter Park Hospital, shopping on Park Avenue, Rollins College, Valencia, Full Sail and UCF. This pet friendly community and charming condo has everything you need! Great opportunity to own in FOUR SEASONS condominiums where LOCATION, LOCATION, LOCATION is prime!

200 Saint Andrews Boulevard Unit 2904, Winter Park
$259,000
3 Beds ⋅ 3 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Welcome to 2433 Grand Teton Circle in the sought-after Cedarwood Village community of Winter Park, where move-in ready living, thoughtful updates, and an unbeatable location come together. Featuring the largest floor plan in the community, this spacious condo has been refreshed with brand-new carpet and fresh interior paint, offering a bright, inviting space that’s ready for its next owner. The highly desirable layout includes a first-floor primary suite, making everyday living both comfortable and convenient. Inside, you’ll love the soaring vaulted ceilings that create an open, airy feel, while the wood-burning fireplace serves as the focal point of the living room, adding warmth and character. Just off the primary suite, a private front patio provides the perfect place to enjoy your morning coffee or unwind in the evening. A dedicated storage room offers additional space for seasonal décor, bicycles, and outdoor equipment. Cedarwood Village is known for its low-maintenance lifestyle, with the HOA maintaining the grounds and completing roof and exterior paint replacements approximately five years ago. Residents also enjoy access to a community pool, clubhouse, tennis courts, pickleball courts and guest parking. Location is one of this home’s greatest features. Ideally situated near Downtown Winter Park, Park Avenue, Winter Park Village, Baldwin Park, Full Sail University, Rollins College, Valencia College, and the University of Central Florida (UCF), you’ll enjoy convenient access to some of Central Florida’s best shopping, dining, entertainment, and recreation. Commuting is easy with nearby Howell Branch Road, Semoran Boulevard (SR 436), Aloma Avenue (SR 426), 417, and I4, providing quick access to Downtown Orlando, Maitland, Lake Mary, AdventHealth Winter Park, and Orlando International Airport. Located within the Seminole County Public School district, this home offers both convenience and an exceptional Winter Park address. Whether you’re searching for a primary residence, a low-maintenance home, or a spacious Winter Park condo in one of Central Florida’s most convenient locations, 2433 Grand Teton Circle offers the perfect combination of space, comfort, and lifestyle.

2433 Grand Teton Circle, Winter Park
$525,000
3 Beds ⋅ 4 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code
Beneath mature oak trees in The Quarters at Winter Park, this townhome-style condominium presents a rare opportunity to own a spacious, architecturally distinctive residence in one of Winter Park's most established communities. Priced to reflect its as-is condition, the home offers exceptional potential for a buyer ready to personalize the space. A gated brick courtyard and covered front porch lead to light-filled living and dining areas featuring engineered hardwood flooring and a wrought-iron staircase. The kitchen offers granite countertops, a gas range and opens to the family room, where a gas fireplace and skylight create a welcoming gathering space. A private screened courtyard connects the residence to the detached two-car garage. Upstairs, the primary suite spans more than 300 square feet and features a custom walk-in closet and dual-sink en-suite bath. Two additional bedrooms include one with a private en-suite bath and another with access to a balcony overlooking the tree-lined street. Ideally just minutes from Park Avenue, Rollins College and Seven Oaks Park, this residence offers the opportunity to renovate and customize a home in one of Winter Park's most sought-after communities. Sold as is, with an inspection report available upon request.

1134 Washington Avenue Unit 13C, Winter Park
$169,900
1 Beds ⋅ 1 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
PRICE ADJUSTMENT! Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping! One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional Built-in Closets, Vanity and Mirrored Closets and updated Bath, accessible for Guests and close to Master! Updated Windows! Private Balcony! Owner is providing a One-Year Home Warranty and a $3,000 Flooring Credit. Make this affordable Unit your own!

1500 Gay Road Unit 4D, Winter Park
$750,000
4 Beds ⋅ 3 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code
Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office or a fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic trails and private access to Lake Howell. The community is also conveniently located near local favorites, including Kelly's Ice Cream, Foxtail Coffee and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.

1418 Lone Feather Trail, Winter Park
$280,000
2 Beds ⋅ 2 Baths ⋅ Lazy Oaks Condo SubDv. ⋅ 32792 Zip Code
Charming two-bedroom, two-bath condominium available in Winter Park. The reserve is fully funded, and monthly condominium fees are low. A comfortable foyer welcomes you inside, leading down the hallway to the second bedroom at the front of the home, where a large window overlooks the front green space. The kitchen opens to a bright, inviting space with skylights that bring natural light into the combined living and dining area. A fireplace adds warmth to the room, while sliding glass doors lead to a private screened enclosure overlooking additional green space at the rear of the property. Ideally positioned within the home, the kitchen features all-new appliances and an oversized pantry with spice shelving for easy organization. The primary bedroom offers an inviting entrance with closet space upon entry. Sliding glass doors fill the room with soft natural light, creating a calm and peaceful atmosphere. The primary bath includes a double vanity and additional deep closet space. From the bedroom, step out to the screened enclosure and enjoy quiet moments in the Florida breeze. Lazy Oaks Condominium is a charming, peaceful community in Winter Park. Conveniently located near shopping, restaurants, schools, and universities, it offers an inviting place to relax and call home.

5184 Lazy Oaks Drive, Winter Park
$285,000
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland. This inviting home features a versatile upstairs loft overlooking the living and dining areas—perfect for a home office, fitness space, craft room, or additional guest accommodations. The bright, cheerful eat-in kitchen is both stylish and functional, showcasing quartz countertops, a glass tile backsplash, abundant cabinetry, a pull-out spice rack, trash/recycling cabinet, and a built-in storage unit. Sliding glass doors open to the private front courtyard, filling the space with natural light. Conveniently located laundry area, complete with washer and dryer, is tucked within the kitchen. The spacious living room features a cozy wood-burning fireplace and flows seamlessly into the dining area beneath soaring vaulted ceilings accented by skylights. Sliding glass doors lead to a screened lanai with a slate tile floor and a storage closet—an ideal spot to relax and enjoy Florida living. The primary suite also opens directly to the lanai and offers a beautifully renovated en-suite bath with a luxurious walk-in shower, updated vanity, linen cabinet, and a custom walk-in closet with built-in organizers. The front bedroom also includes a generous walk-in closet. Enjoy added privacy with a picturesque, tree-lined green space across the street rather than neighboring condos directly in front. Two dedicated parking spaces are conveniently located just outside your door. Cedarwood Village offers an exceptional location directly across from Casselberry Commons Shopping Plaza and is just minutes from Full Sail University, UCF, and Rollins College. Residents enjoy a community swimming pool, tennis courts with pickleball lines, and designated dog-walking areas. Additional highlights include a new roof and skylights installed in 2020. Monthly HOA fees cover exterior maintenance, lawn care, and community amenities, making this the perfect opportunity to enjoy carefree living in one of the area's most desirable communities.

2372 Sun Valley Circle Unit 2372, 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
$350,000
3 Beds ⋅ 3 Baths ⋅ Vistas At Lake Howell SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully maintained townhome located in the heart of Winter Park, Florida. From the moment you arrive, the charming exterior draws you in with its classic stucco finish, attached one-car garage, manicured landscaping, and a welcoming shaded entry framing the front door. Step inside to an inviting foyer featuring high ceilings, modern lighting, and a striking staircase that sets a stylish tone for the rest of the home. The main level transitions into an expansive, light-filled open concept floor plan seamlessly connecting the living room, dining area, and kitchen. Rich wood-look LVP flooring runs throughout the entire lower level, perfectly complementing the crisp neutral walls and providing a cohesive, contemporary aesthetic. The spacious living and dining areas offer an exceptional layout for both daily living and effortless entertaining. Large sliding glass doors at the rear of the home flood the living space with natural light and open directly to a private, screened-in back patio, making it easy to enjoy the Florida breeze. Overlooking the dining area is a spacious kitchen, which features a half-wall cutout that keeps the chef connected to the conversation. Equipped with plenty of warm wood cabinetry, neutral countertops, a deep double sink, and a suite of white appliances, this kitchen is as ample as it is welcoming. A convenient guest half-bathroom with a pedestal sink completes the well-designed ground floor layout. Head upstairs to discover the private living quarters, where the beautiful wood-look flooring continues through the hallway and into each spacious bedroom. The expansive primary suite serves as a true retreat, boasting high vaulted ceilings, an elegant modern ceiling fan, a massive walk-in closet with built-in wire shelving, and a trio of large windows that fill the space with cheerful morning light. This main bedroom easily accommodates king-sized furniture and offers the luxury of an attached en-suite bathroom with dual sinks. The additional bedrooms are equally impressive, each featuring soaring vaulted ceilings, updated stylish ceiling fans, and generous closet space near the dedicated upper-level laundry closet, which comes equipped with a washer and dryer. The outdoor and utility spaces add tremendous value and convenience to this efficient property. The attached garage features an open, clean layout perfect for secure parking, extra storage, or a small home workshop area. At the back of the home, the deep screened-in patio is an ideal spot for outdoor dining, grilling, or relaxing in the shade. The patio steps out onto a beautiful community green belt with pristine lawns and mature shade trees, offering a peaceful residential backdrop. Nestled in a premium, tree-lined enclave, the community boasts pristine, winding roads, manicured privacy hedges, and a scenic retention pond complete with a flowing water fountain feature. This idyllic neighborhood setting perfectly balances the tranquility of nature with outstanding proximity to nearby lakes, parks, major roadways, and local shopping centers. Don't miss the opportunity to own this pristine, move-in ready retreat in one of Central Florida's most highly sought-after locations.

2521 Galliano Circle, 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
$299,999
3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code
Enjoy abundant natural light throughout this beautifully maintained one-story, 3-bedroom, 2-bath home, enhanced by soaring vaulted ceilings and an inviting open layout. The kitchen features natural wood cabinetry, stainless steel appliances, and a charming breakfast nook with access to the front patio. The spacious primary suite offers a walk-in closet and private access to the patio. A desirable split-bedroom floor plan provides added privacy, with two guest bedrooms and a full guest bath situated at the front of the home. The bright and versatile patio can be accessed from both the living room and primary suite, creating the perfect space to relax, entertain, or enjoy year-round Florida living. Roof 2023, A/C 2020, Water Heater 2020, pex piping upgrades include pavered driveway, bathrooms updated, patio doors updated, and vinyl fencing in backyard.

2339 Inagua Way, Winter Park
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