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$699,000
4 Beds ⋅ 2 Baths ⋅ 12747205 MLS ⋅ ACTIVE Status
Welcome to Highwood on the North Shore! This approximately 1,904-square-foot Lannon Stone ranch offers flexible living space, hardwood floors throughout, and two fireplaces that add warmth and character. The spacious, and light filled living room overlooks a beautiful park, while the separate dining room with rich slate flooring opens to the patio and connects to the kitchen. The house has generous closet space throughout with an attic running the length of the house for additional storage. The home features two bedrooms, a full hall bath, and a versatile paneled den that can alternatively serve as a home office, family room, or additional bedroom. A private three-room in-law suite provides excellent flexibility for extended family, guests, or integration into the main living space. Outside, enjoy a large, private fenced backyard ideal for entertaining, gardening, or relaxing. The attached two-car garage plus an additional detached two-car garage provide abundant parking and storage. Situated on a desirable oversize corner lot this home is just minutes from downtown Highwood, Metra service, popular restaurants, and Lake Michigan. Being sold "AS-IS" as part of an Estate, this is a unique opportunity to update, personalize, and make this home your own in the most sought after area of Highwood.

27 Pleasant Avenue, Highwood
$1,295,000
3 Beds ⋅ 4 Baths ⋅ 12716039 MLS ⋅ ACTIVE Status
NEW CONSTRUCTION WITH FIRST FLOOR PRIMARY crafted with impeccable attention to detail, 251 High Street offers modern luxury across three levels of beautifully finished living space. The open-concept main level boasts soaring ceilings, wide-plank floors, and a light-filled living room anchored by a custom fireplace. The chef's kitchen is a true centerpiece, featuring high-end stainless steel appliances, custom cabinetry, and a dramatic waterfall island. The main level primary suite serves as a private retreat, featuring dual closets and a spa-inspired ensuite bath with heated floors, a double vanity, extensive custom tile, and an oversized walk-in shower. Main-floor convenience continues with a dedicated laundry room, mudroom, and a stylish powder room. Upstairs, find two spacious bedrooms sharing a beautifully appointed hall bath. The fully finished lower level with high ceilings boasts an extraordinary all-glass wine cellar, a huge recreation space with a second fireplace, and a private 4th bedroom with walk-in closets and a full bathroom with an oversized shower. Excellent opportunity to own in a prime location close to Highwood's acclaimed dining, trains, and parks!

251 High Street, Highwood
$550,000
2 Beds ⋅ 2 Baths ⋅ 12727506 MLS ⋅ ACTIVE Status
Totally updated in 2025 and move-in ready, this charming ranch blends single-level living with a fully finished basement - and serious income potential. The main level features an open kitchen with breakfast/office space, a comfortable living room, two bedrooms, and a full bath with walk-in shower, all on beautiful hardwood floors. The finished lower level adds a second full bath with tub, laundry, and a bedroom with attached bonus room - perfect as a second bedroom, nursery, or flex space - with potential for a separate hall entrance, ideal for an Airbnb or short-term rental (check local zoning rules). Updates include new heat/A/C and appliances (2026), sump pump (2025), and roof (2022), plus a brick driveway for three cars and a two-car garage. Turnkey, flexible, and investor-friendly! Available fully furnished! See floor plans to see forth bedroom option. Currently the fourth bedroom is a walk through.

247 Highwood Avenue, Highwood
$549,000
4 Beds ⋅ 2 Baths ⋅ 12654067 MLS ⋅ ACTIVE Status
Calling all investors & rehabbers- fabulous or opportunity for existing ranch style 2 flat in booming Highwood. Each unit is 2 beds, 1 bath, oversized garage parking and tons of storage, laundry in basement. Property is zoned as multi unit, so tear down and built opportunity available- tons of space to develop the land or improve/expand existing property.

124 S Central Avenue, Highwood



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