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$3,390,000
5 Beds 4 Baths
Ideally situated on a private cul-de-sac in Chestnut Hill, this stunning architectural gem offers timeless elegance & modern luxury. Just minutes to the T, restaurants, coffee shops, & shopping, it boasts unobstructed park views from a Bluestone patio with a luxury outdoor kitchen and 8' gas fireplace perfect for entertaining. Inside, enjoy a sauna, home gym, wine cellar, billiards room, & a richly paneled library.First floor offers a radiant living room with fireplace and detailed moldings, a sunroom with three exposures, & a formal dining room with bay windows, original paneling, and wood-burning fireplace.The chef’s kitchen impresses with custom cabinetry and top-of-the-line appliances. Upstairs, the expansive primary suite features a gas fireplace, walk-in closet, and marble bath.Two additional large bedrooms, full bath, office, and laundry complete the second level.The third floor includes a media room, two bedrooms, and a playroom.Heated driveway & luxury systems throughout.

460 Heath Street, Brookline

Listing Courtesy of : Samantha Stumpo ---- Serhant

$3,995,000
5 Beds 6 Baths
This elegant European-style country home is located in one of Old Chestnut Hill’s most desirable neighborhoods, ideal for modern family living and entertaining. The chef’s kitchen opens to a sun-filled family room and connects to both indoor and outdoor dining areas. The first floor also features a spacious living room and cozy library, both with fireplaces. Upstairs, the expansive primary suite includes dual walk-in closets and a luxurious bath with soaking tub and large shower. Four additional bedrooms and two baths complete the second floor. The third floor offers a bright new gym with skylights and a full bath with steam shower. The walk-out garden level includes a playroom, full bath, movie theater with Savant system, and dining area. Beautifully landscaped grounds feature two patios, a large play area, and a heated driveway. Steps to the T, the Chestnut Hill Reservoir, and the shops and restaurants at The Street.

85 Gate House Road, Newton

Listing Courtesy of : Chamberlain Group ---- Coldwell Banker Realty - Brookline

$2,249,000
4 Beds 5 Baths
New construction townhouse-style condo with three levels & over 3,000 SqFt. Single-family space with condo convenience. Brookline schools. 8-inch white oak hardwood throughout. Natural light from every angle. Four bedrooms, each with a custom walk-in closet and en-suite full bath featuring built-in Bluetooth speakers. Quartz counters in kitchen & all bathrooms. Third floor includes dedicated laundry room with washer and dryer installed, plus bonus room ideal for home office, gym, or playroom. Open-concept main level with kitchen, living area, and half bath. Living room walks out to private deck and fenced garden perfect for upcoming spring & summer months. Common garage with automotive turntable and two assigned parking spots. Tiled mudroom entry with additional storage room. Steps from Chestnut Hill Square, The Street, and Chestnut Hill Mall.  HOA covers snow removal, water, sewer, and master insurance. CO in hand, nothing left to do but move in.

811 Heath Street, Brookline

Listing Courtesy of : Yasmeen Moukaddem ---- McCorry Real Estate, LLC

$2,249,000
4 Beds 5 Baths
Brand new construction, townhouse-style condo with over 3,000 SqFt. Single-family space with condo convenience. Brookline schools. 8-inch white oak hardwood throughout. Natural light from every angle. Four bedrooms, each with a custom walk-in closet and en-suite full bath featuring built-in Bluetooth speakers. Quartz counters in kitchen and all bathrooms. Third floor includes dedicated laundry room with washer and dryer installed, plus bonus room ideal for home office, gym, or playroom. Open-concept main level with kitchen, living area, and half bath. Living room walks out to private deck and fenced garden perfect for upcoming spring & summer months. Common garage with automotive turntable and two assigned parking spots. Tiled mudroom entry with additional storage room. Steps from Chestnut Hill Square, The Street, and Chestnut Hill Mall.  HOA covers snow removal, water, sewer, and master insurance. CO in hand, nothing left to do but move in.

809-811 Heath St Unit 811, Brookline

Listing Courtesy of : Yasmeen Moukaddem ---- McCorry Real Estate, LLC

$9,985,000
5 Beds 8 Baths
Set on .74 acres in one of Brookline’s most coveted neighborhoods, this newly constructed estate blends timeless architecture with exceptional modern design. With impeccably finished living spaces and full AV wiring, it offers 5 bedrooms, 6 full and 2 half baths, and a layout ideal for today’s lifestyle. The heart of the home is a showstopping chef’s kitchen with top-tier appliances, custom cabinetry, and a large island opening to sun-filled living and dining areas. A seamless indoor-outdoor flow connects to the private, flat tree-lined lot—perfect for entertaining or relaxation. Highlights include a luxurious primary suite with spa bath, generous secondary bedrooms, family room and a versatile finished lower level, attached 3-car garage with heated driveway, permitting for a pool. Built by a renowned local builder, this move-in-ready residence offers unmatched style, craftsmanship, and comfort in one of Brookline’s most desirable settings. Just bring your toothbrush!

68 Clyde Street, Brookline

Listing Courtesy of : Maggie Gold Seelig ---- MGS Group Real Estate LTD

$5,627,000
9 Beds 6 Baths
Once-in-a-lifetime opportunity in Olde Chestnut Hill - this grand turn of the century victorian home is situated on almost 1 acre and offers mature trees and plantings, a large private back yard, and a separate 2+ car barn. Walking distance to many area amenities and public transportation, this elegant home is perfectly sighted away from the street and offers supreme privacy. Many restored historical details include a formal foyer with grand staircase, multiple fireplaces, and reclaimed hardwood flooring. Flooded with natural light this gracious home offers a large eat-in kitchen that overlooks the back yard, a banquet sized formal dining room, and a double parlor that is ideal for entertaining. The second floor of the home is complete with 4+ bedrooms, including a bright primary bedroom with en suite bath and study. The top floor boasts 3+ bedroom, large laundry room. Abundant storage throughout, partially finished basement, plus an outdoor covered loggia in the heart of Chestnut Hill

394 Hammond St, Newton

Listing Courtesy of : Michael Harper ---- Coldwell Banker Realty - Boston

$16,980,000
7 Beds 11 Baths
Introducing Paine Estate, a grand Georgian Revival architectural treasure located in the highly coveted Chestnut Hill neighborhood of Brookline. This outstanding property has been extensively renovated, now combining traditional style and modern amenities with a thoughtful floor plan ideal for comfortable family living and grand entertaining. Exceptional features include a grand entry hall, elegant formal sunken living room overlooking the picturesque gardens, fireplaced dining room, gourmet chef's kitchen, family room, handsome wood paneled library and an expansive great room. 6 bedrooms include the luxurious primary suite complete with separate bathrooms and dressing rooms and balcony. Additional features include a mudroom, exercise/club room, au-pair suite and wine cellar. This majestic home is surrounded by over 2 acres of beautifully landscaped grounds featuring an outside kitchen and dining area, a formal parterre garden and plunge pool. Magnificent opportunity not to be missed!

1014 Boylston Street, Brookline

Listing Courtesy of : Tracy Campion ---- Campion & Company Fine Homes Real Estate

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