Winter Park Pines Homes with No Deed Restriction Community Extras

Winter Park Pines Homes with No Deed Restriction Community Extras

Welcome to Winter Park Pines, a hidden gem nestled in the heart of Winter Park, Florida. This charming subdivision, located in Orange County, offers a perfect blend of suburban tranquility and vibrant community life. Known for its lush landscapes and picturesque streets, Winter Park Pines is an ideal choice for families, retirees, and anyone seeking a peaceful retreat with easy access to urban conveniences.

One of the standout features of Winter Park Pines is its unique status as a community with no deed restrictions. This means homeowners enjoy the freedom to personalize their properties and create their dream homes without the constraints often found in more regulated neighborhoods. Whether you envision a flourishing garden, a custom outdoor space, or perhaps a workshop for your hobbies, the possibilities are endless here.

The homes in Winter Park Pines are diverse, ranging from charming single-family residences to modern builds, catering to a variety of tastes and lifestyles. Many properties boast spacious yards, perfect for outdoor gatherings, children’s play, or simply soaking in the Florida sunshine.

Beyond the homes, the community offers a wealth of amenities and nearby attractions. Enjoy leisurely strolls through the scenic parks, or take advantage of the proximity to downtown Winter Park, where you can explore boutique shops, delightful eateries, and cultural landmarks. With excellent schools and a friendly atmosphere, Winter Park Pines is not just a place to live; it’s a place to thrive. Discover your new home in this welcoming community today!

Newest Winter Park Pines Homes with No Deed Restriction Community Extras

518 Gilbert Road, Winter Park
$649,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Welcome to 518 Gilbert Road, a beautifully updated 3-bedroom, 2-bath pool home offering 1,573 square feet of single-story living in the desirable Winter Park Pines neighborhood - with no HOA. Freshly installed front yard sod and mulch, mature palms, and distinctive stone accents create an inviting first impression. Inside, the home is light and bright with original terrazzo flooring and spacious living and dining areas. The living room features a wood-burning fireplace and architectural ceiling detail that adds character to the space. The beautifully updated kitchen offers white cabinetry, granite countertops, stainless steel appliances, a gas cooktop, convection oven, subway tile backsplash, modern lighting, and a large peninsula with bar seating. Both bathrooms have been renovated, including the primary bath with a walk-in shower and an updated guest/pool bath with convenient direct access to the backyard. Step outside to a private screened pool and an expansive pool deck, recently resurfaced in May 2026, providing plenty of room for outdoor dining, entertaining, and relaxing. Fully paid solar pool-heating panels extend the enjoyment of the pool, while the fully fenced PVC backyard adds privacy. A spacious two-car garage and outdoor storage provide additional room for everyday needs. Additional improvements include updated windows and sliding doors, replumbing, a newer HVAC system with gas/propane furnace, gas line, and partial updated ductwork. Enjoy an exceptional Winter Park location close to Cady Way Trail, Winter Park Pines Golf Club, Cady Way Park and its recreational amenities, Baldwin Park, and Downtown Winter Park. AdventHealth Winter Park, Rollins College, Full Sail University, UCF, shopping, dining, and everyday conveniences are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School, this move-in-ready pool home combines classic Winter Park character, thoughtful updates, and an outstanding location.

518 Gilbert Road, Winter Park
266 N Ranger Boulevard, Winter Park
$724,900
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
FULLY RENOVATED Winter Park Pines Home with Mother-in-Law Suite, NO HOA & Prime Location! Welcome to this beautifully transformed Winter Park Pines residence, where modern design, thoughtful upgrades, and flexible living spaces come together in one exceptional home. Ideally located adjacent to the Cady Way Trail, with NO HOA, this property offers the lifestyle and convenience of Winter Park with the flexibility today’s buyers are looking for. Upon entering, you’re greeted by a dramatic custom charcoal accent wall with geometric detailing, creating a distinctive architectural focal point and setting the tone for the home’s contemporary design. Inside, the open and inviting floor plan features Luxury Vinyl Plank flooring throughout, recessed LED lighting, all-new interior doors, and a stylish LED fireplace that adds warmth and ambiance to the main living area. The completely renovated kitchen is designed for both everyday living and entertaining, featuring new Shaker-style cabinetry, Quartz countertops, a large center island, luxury backsplash, stainless-steel appliances, and a dedicated coffee bar with wine refrigerator. The open layout provides an ideal gathering space for family and guests. The home also features a private Mother-in-Law Suite with its own entry and outside walkway, offering exceptional flexibility for extended family, overnight guests, a home office, or a private living area. The suite includes its own beautifully renovated bathroom with a rain shower, enclosed by a ceiling-to-threshold glass pane, and an illuminated LED mirror. The primary suite bathroom has been upgraded to a luxurious, contemporary retreat, featuring a smart toilet, dual vanities, illuminated LED mirror, and an executive-style stand-up rain shower. The shower incorporates a thoughtfully designed inclined floor that directs water into a rectangular drain, along with a striking floor-to-ceiling glass enclosure, creating a clean, open, and refined feel without the need for a traditional shower curtain. Additional major improvements include a new Carrier HVAC system, tankless water heater, updated double-pane windows, complete re-plumbing, re-wiring with an updated electrical panel, and a new roof installed 7/17/2023. Step outside and enjoy the home’s inviting outdoor spaces, including a covered front porch with dusk lighting, screened rear porch, spacious backyard, and oversized driveway. A series of cement slab walkways, separated by polished, large river stones, leads from the garage to the front door, with matching paths continuing along the rear of the home. Solar security lighting and decorative LED lighting add both functionality and evening ambiance. Ideally situated in Winter Park Pines and directly adjacent to the Cady Way Trail, the home offers convenient access to major roadways, hospitals, golf courses, colleges, shopping, dining, and highly regarded private schools—all within a short drive. With an extensive renovation, three beautifully updated bathrooms, a private Mother-in-Law Suite, modern kitchen, tankless water heater, new roof, updated electrical and plumbing, NO HOA, and an outstanding Winter Park location, this home offers a rare combination of style, functionality, and convenience. Come experience the renovation, thoughtful details, and flexible floor plan in person. Schedule your private showing today!

266 N Ranger Boulevard, Winter Park
274 N Ranger Boulevard, Winter Park
$659,900
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Bright, airy, and designed for a resort living! Welcome to a turn-key Winter Park Pine home where everyday life feels like a getaway! From the moment you enter, you will appreciate the home's refined modern aesthetic, clean architectural lines, and thoughtfully curated finishes. Brand new flooring creates a seamless sense of elegance throughout, while sleek new cabinetry, contemporary finishes, and new premium appliances, and new quartz counters is suited for dinning or entertaining! Through brand-new sliding glass doors lies the crown jewel: a sparkling, screened in-ground pool surrounded by a luxury private patio! Spend time hosting barbecues under the covered lanai or relaxing in the warm afternoon sun! Yard is fully fenced and sitting in a large corner lot! Private backyard featuring a plenty sitting areas and a brand-new fire pit for wonderful outdoor gatherings! Brand-new Roof, water heater and AC in 2024 for a comfortable living! Whether you are doing morning exercise or watching the sunset by the water, it delivers a peaceful resort living! Living in this renown Winter Park Pine neighborhood with No HOA, yet easy access to golf courses, biking trails and parks, community amenities, Advent hospital, Park Ave, Rollin College and Baldwin Park! Renown school districts and convenient locations! Don't miss out on this rare find—call now to see it in person!

274 N Ranger Boulevard, Winter Park
724 Monmouth Way, Winter Park
$759,675
5 Beds ⋅ 4 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Pictures simply do not convey the beauty and feel of true ‘Sanctuary’ in this beautifully and breath-taking renovation! One of the biggest houses in Winter Park Pines and the only house in the community with a full kitchen butler's pantry. Spatially designed and updated for modern family living with separate bedroom wings for privacy, it also features quiet areas for contemplation and large areas for gatherings. It’s a hard choice of which is more impressive, the classic white kitchen with an open 9’x5’ island and 11’ butler's pantry featuring a 2nd sink and additional refrigerator, or the magazine-worthy design of the spacious Primary Bath. You get to choose! The Primary bedroom space (13x22) qualifies as a true retreat. All of this in the beauty of an established neighborhood on a quiet street where you can walk to the Winter Park Pines golf course, or take in many recreational opportunities the area has to offer (Cady Way Trail, Cady Way Pool, sports courts and ball fields galore) as well as a top-ranked hospital and healthcare facilities (Crosby Wellness Center or WP YMCA). Relax, the 2026 renovation has you covered for many years: New Roof, New wiring, New plumbing and water heater. The HVAC was new in 2019. Beautiful floors and fresh paint complete the package that is a rare find in such a fabulous location. Hurry! This one should be at the top of your list.

724 Monmouth Way, Winter Park
722 S Ranger Boulevard, Winter Park
$775,000
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
” TURN-KEY,” “PRIVATE POOL,” “NO HOA,” “RENOVATED,” and “POSSIBLE ADU Welcome to this beautifully renovated 4-bedroom, 3-bathroom home where modern updates, exceptional outdoor living, and true pride of ownership come together. Move-in ready and designed for effortless Florida living, this home offers an incredible combination of style, comfort, and flexibility. Engineered wood floorings & tile throughout, no carpets to clean! Everything for a 4.0 Inspection has an updated permit with warranty! A NEW ELECTRIC PANEL(2026), WATER HEATER,(2024) HVAC (2024) all NEW PEX PIPING (Oct 26)& ROOF with transferrable warranty. CUSTOM painted kitchen cabinets with granite countertops & backsplash and numerous additional improvements that make this home truly turn-key. The open, inviting layout flows seamlessly toward the spectacular backyard, where a kitchen pass-through window opens directly to the expansive covered SCREENED (2026) patio, creating the perfect setup for entertaining family and friends. Step outside to your own private resort-style backyard oasis! The freshly RESURFACED swimming pool, CUSTOM beautiful NEW PAVERS with OUTDOOR SHOWER sets the stage for relaxing afternoons and memorable gatherings. A large PERGOLA, generous covered outdoor living space, & LARGE YARD make this backyard the ultimate retreat for enjoying the Florida lifestyle year-round. Great potential for an ADU/guest suite, (subject to zoning and county approval). PRIVATE WELL for irrigation (front yard) & EPOXY garage floor. Location is another standout! Zoned for highly rated schools with Winter Park High just one mile away. Conveniently located near Cady Way Park & trails, Winter Park Pines Golf Course, Rollins College, UCF, and Full Sail University. Enjoy easy access to the dining, shopping, and entertainment of Park Avenue, just approximately 4 miles away.

722 S Ranger Boulevard, Winter Park
715 S Ranger Boulevard, Winter Park
$695,000
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Welcome to your dream home in the highly sought-after community of Winter Park Pines! This beautifully maintained 4-bedroom, 3-bathroom residence offers 2,312 square feet of comfortable and stylish living space ideally designed for modern and multigenerational lifestyles. The recently remodeled primary suite is a true retreat, featuring new carpeting and tile flooring, dual granite vanities, an oversized walk-in shower with modern, upgraded fixtures, a new water closet, and thoughtful contemporary finishes throughout. Inside, you’ll find timeless architectural charm which includes a formal dining room, three spacious living areas, louvered window shutters, and elegant hardwood flooring. One of the living spaces is highlighted by a stunning brick fireplace overlooking the beautiful private pool area and fully fenced backyard — creating the perfect setting for entertaining, family gatherings, or simply unwinding in your own backyard oasis. In addition, this spectacular residence also boasts tasteful landscaping touches for exceptional curb appeal, a large two-car garage with electric opener, a newer shingle roof replaced in late 2023, and fresh interior paint throughout the home. Ideally located near Winter Park Pines Golf Club, Cady Way Trail, Ward Park, Showalter Field, tennis and pickleball courts, top-rated schools, and the many shopping and dining destinations of Park Avenue and historic downtown Winter Park. Don’t miss this rare opportunity to own a true Winter Park gem — schedule your private showing today!

715 S Ranger Boulevard, Winter Park
2758 Banchory Road, Winter Park
$619,500
3 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
FULLY PAID SOLAR PANELS INCLUDED — NO SOLAR LOAN TO ASSUME! A rare added value for the next owner: enjoy the benefits of solar energy with the system included in the sale and no remaining solar panel balance. Welcome to 2758 Banchory Rd, a beautifully maintained 3-bedroom, 2-bath pool home in desirable Winter Park Pines. This charming ranch-style home offers a bright open layout, mature landscaping, a fully fenced backyard, private swimming pool, covered outdoor living space, storage shed, and no HOA. Located just steps from the Cady Way Trail and minutes from Cady Way Park, Winter Pines Golf Club, Baldwin Park, AdventHealth Winter Park, Full Sail University, Downtown Winter Park and Park Avenue. Enjoy the privacy of a quiet street with convenient access to shopping, dining, recreation and major roadways. PRIVATE POOL + PAID-OFF SOLAR + NO HOA + PRIME WINTER PARK LOCATION. An exceptional combination of lifestyle, location and long-term value. Schedule your private showing today.

2758 Banchory Road, Winter Park
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