Winter Park Pines Homes under $750,000

Winter Park Pines Homes under $750,000

Welcome to Winter Park Pines, a charming subdivision nestled in the heart of Winter Park, Florida. This vibrant community is known for its picturesque landscapes, friendly atmosphere, and convenient access to the best that Central Florida has to offer. Located in Orange County, Winter Park Pines is an ideal destination for families, retirees, and anyone seeking a tranquil yet engaging lifestyle.

One of the standout features of Winter Park Pines is its diverse selection of homes, with many options available for under $750,000. This makes it an attractive choice for first-time buyers, young families, and those looking to downsize without compromising on quality or comfort. Homes in this subdivision often boast modern designs, spacious layouts, and well-maintained yards, perfect for outdoor gatherings or quiet evenings under the stars.

Residents of Winter Park Pines enjoy a wealth of amenities, including nearby parks, walking trails, and recreational facilities. The community is also just a short drive away from the charming downtown Winter Park, where you'll find delightful boutiques, art galleries, and an array of dining options. The area is well-regarded for its top-rated schools and close-knit community feel, making it a wonderful place to call home.

If you’re searching for a beautiful home in a welcoming neighborhood, Winter Park Pines offers an exceptional blend of comfort, convenience, and affordability. Discover your new beginning in this delightful subdivision, where your dream home awaits!

Newest Winter Park Pines Homes under $750,000

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
433 Gilbert Road, Winter Park
$669,900
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
A RARE SECOND CHANCE IN WINTER PARK PINES! This beautifully updated three-bedroom, two-bath POOL home is available again, giving one fortunate buyer another opportunity to make it theirs. This beautifully updated and spacious home, offering nearly 1,800 square feet of thoughtfully designed living space on a spacious lot backing to a peaceful conservation easement. Featuring separate living and family rooms, a remodeled kitchen, and an exceptional outdoor retreat, this inviting home is perfectly designed for both everyday living and entertaining. From the moment you arrive, the classic brick entry creates a warm first impression. Inside, the flexible floor plan provides plenty of space to gather, relax, work from home, or host guests. Laminate wood flooring and updated baseboards (2022) complement plantation shutters, recessed lighting, and ceiling fans throughout. Multiple storage closets add everyday functionality, while updated windows and French doors fill the home with natural light and seamlessly connect the indoor and outdoor living spaces. The remodeled kitchen (2021) features crisp white shaker cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, an oversized stainless-steel sink, and a breakfast bar with seating for four. A dedicated coffee bar and pantry add convenience, while the large bay window overlooks the pool and private backyard, creating the perfect backdrop for everyday living. The spacious primary suite offers a walk-in closet and ceiling fan. Its ensuite bathroom, renovated in 2022, features large marble-look tile, a double vanity with quartz countertops, and a beautifully updated walk-in shower with a frameless glass enclosure. Two additional guest bedrooms and an updated full bathroom complete the bedroom wing. Step outside to the true centerpiece of the home. Backing to a conservation easement, the backyard offers a peaceful setting with enhanced privacy. The screened, in-ground chlorine pool was completely refreshed in 2025 with new tile, resurfaced, and new pool light. The lanai deck was also resurfaced, creating an ideal space for swimming, outdoor dining, and entertaining family and friends. The outdoor improvements continue with fresh landscaping completed in 2025, including new sod, a stone pathway, French drains for improved drainage, and an updated irrigation timer. The fully fenced backyard (2023) provides additional privacy for pets, play, and gatherings. Ideally located near Cady Way Trail and Winter Park Pines Golf Course, you'll also enjoy convenient access to Cady Way Park amenities, including a community pool, playground, tennis and pickleball courts, beach volleyball, and walking trails. Less than 10 minute drive to Park Ave luxury shopping and dining experiences. AdventHealth Winter Park and the Crosby Wellness Center are just minutes away, while Rollins College, Full Sail University, UCF, and Orlando International Airport are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines modern updates, flexible living spaces, and a private backyard retreat in one of Winter Park's most desirable locations. ROOF - 2024, ELECTRICAL PANEL - 2021, HVAC - 12/1997

433 Gilbert Road, 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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