Refine Search
Map
Sort by
$1,125,000
3 Beds ⋅ 3 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Virtually Staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome you into the main living space, while the showpiece kitchen delivers true chef-level design with new Custom European Cabinetry, Quartz Countertops with a Waterfall Island, Porcelain Tile floors, premium lighting, under counter Kitchen Aid Ice Maker and a top-tier appliance suite including Wolf Gas Range-top, Wolf Built-in Oven & Microwave and Bosch Refrigerator and Dishwasher. The primary suite is a serene retreat with a newly redesigned spa style bath with frameless walk-in shower, soaking tub, new double sink vanity and lighting—plus a walk-in closet with California Closet built-in’s and a versatile bonus room ideal for a sitting area, nursery, or additional laundry space. Outdoors, enjoy resort-style living under the expansive 26’ x 24’ covered Lanai featuring vaulted tongue-and-groove ceilings, tile flooring, a striking stone gas fireplace with RealFyre burners, stainless mantle, perfect for effortless entertaining. There is even enough room to customize the outdoor space with your own Pool Oasis. Recent improvements include Roof 2020, New HVAC System, New Double-Pane windows, 4-panel slider & front door, fresh interior/exterior paint, new custom shades, privacy bamboo landscaping, privacy fencing and an extended paver driveway. The attached Garage offers dedicated storage space and a bonus room with mini-split system which could offer space for home gym or office. Just minutes from Park Avenue’s acclaimed dining and shopping, top Winter Park amenities, Advent Health Medical Campus and quick access to key corridors for an easy downtown Orlando commute, this is 32789 living at its most refined—classic architecture, modern systems, and elevated indoor-outdoor lifestyle in one of Winter Park’s most sought-after neighborhoods.

1651 Westchester Avenue, Winter Park
$810,000
2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Lovely Orwin Manor home with custom pool and spa in the heart of Winter Park. Backyard oasis features a detached guest house (ADU) with a kitchenette, bathroom and two built-in murphy beds.

1314 Canterbury Road, Winter Park
$771,000
3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
You know it's going to be a winner when the primary walk-in-closet, alone, is 8'x10'! This beautiful Orwin Manor home has it all: 3 bedrooms, 2 bathrooms, and indoor laundry room, updated kitchen and baths, a detached 1 car garage, flex space for a playroom or office, and incredible systems updates like a 2018 roof, 2020 water heater, and 2022 HVAC. Once you get past the beautiful curb appeal, you'll step into a multifunctional living space with options for living and dining. You'll appreciate the split plan layout with two secondary bedrooms in one hallway and an expansive primary suite in the back of the home. All of the bedrooms have freshly cleaned carpet and the living spaces in the home are a versatile engineered hardwood. The kitchen, complete with dry bar and wine storage, is in the middle of the home making for easy entertaining and it's filled with convenient storage! Out back, enjoy the well-maintained yard space and 1 car garage for parking and/or storage. The location is ideal, as it's centrally located to the best of both Winter Park and Orlando. Less than a mile from Foxtail Coffee and Kelly's Ice Cream on Orange Ave, 1.5 miles from Rollins College, less than 2 miles from Publix, and so much more.

1340 Pelham Road, Winter Park
$625,000
3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Welcome to this beautifully renovated historic home in the heart of Orwin Manor, one of Winter Park’s most treasured neighborhoods. Thoughtfully updated while preserving its timeless character, this 3 bedroom 1 and a half bath home blends classic architectural charm with today’s modern conveniences. Major system improvements include updated plumbing and electrical, a new roof in 2025, new HVAC in 2025, exterior painting completed in 2024, original hardwood floors, hot water heater within the last two years, and much more offering true peace of mind for years to come. The inviting renovated kitchen features updated cabinetry, granite surfaces, stainless steel appliances, and a spacious island perfect for everyday living and entertaining. A generous 18’ x 16’ screened porch expands the living space and overlooks a lush, beautifully curated garden, creating a serene indoor-outdoor retreat. All bedrooms are spacious outfitted with built-in closets, beautiful updated windows and blinds. An added bonus is the electric vehicle charging station with driveway privacy gate, ideal for modern lifestyles. This property is individually registered on the City of Winter Park Historic Registry, a rare distinction that celebrates its architectural significance and heritage. The home has been meticulously cared for and retains the warmth and craftsmanship that make historic properties so special. Orwin Manor offers an unbeatable location between Winter Park, College Park, and Downtown Orlando just minutes from AdventHealth, Loch Haven Park, the Orlando Museum of Art, Orlando Science Center, and multiple theaters. Enjoy easy access to Park Avenue, Ivanhoe Village, and Mills Park, all filled with exceptional dining and boutique shopping, with convenient routes that avoid I-4 when desired. A true blend of history, beauty, and modern living, this is a home you’ll fall in love with the moment you arrive. Schedule your private showing to experience this beautiful home today!

1500 Berkshire Avenue, Winter Park
$530,000
2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32803 Zip Code
Welcome to this beautifully updated 2-bedroom, 2-bathroom home in the highly sought-after Orwin Manor. Known for its mature oak-lined streets and unbeatable location, Orwin Manor offers close proximity to Mills 50, Park Avenue in Winter Park, local parks, cultural attractions, AdventHealth, SunRail, and downtown Orlando’s dining and entertainment. Step inside to an inviting open floor plan that seamlessly connects the living room, dining area, and kitchen, all overlooking the spacious covered and screened-in porch, open wood deck, and fully fenced backyard. This layout is ideal for both everyday living and effortless entertaining. The kitchen features solid wood cabinetry, updated granite countertops, and stainless steel appliances. Real wood floors run throughout the living areas and bedrooms, transitioning smoothly into new porcelain wood-plank tile in the dining room and kitchen for durability and style. The spacious primary suite offers direct access to the back porch, creating a private retreat, along with a walk in closet, separate bathtub, updated shower, and dual vanity. Major system upgrades provide peace of mind, including: Roof (2023), HVAC (2022), full re-plumb (2023), rear wood deck (2021), Landscaping & irrigation (2025), double pane windows & a beautiful brick paver driveway and front porch. Plus a one car garage for additional parking or storage. This move-in ready home combines timeless character with thoughtful improvements — all in one of Orlando’s most desirable established neighborhoods.

3258 N Orange Avenue, Orlando
$479,000
2 Beds ⋅ 1 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Beautiful piece of property on Clay St. in Winter Park. Fantastic location. Nearly a third of an acre. Minutes to downtown Winter Park , Advent Health medical center on Rollins St. and Dubsdread golf course. *Double gate fence for boat or RV. *Newer A/C in 2017. *Newer roof in 2017. *Garage *Huge fenced-in backyard. *Wood floors. Enjoy this home or build new on this great piece of property. Come and imagine the possibilities. What's your offer?

1386 Clay Street, Winter Park
$470,000
2 Beds ⋅ 1 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Nice 2BR/1Bath plus office/nursery in the heart of Orwin Manor.

1564 Cavendish Road, Winter Park