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$859,900
3 Beds 3 Baths ACTIVE Status 24205672 MLS
Own a Piece of History! This bucolic Brookfield beauty offers a rare combination of history, character, land, and opportunity. Built in 1775, this Antique Colonial has watched over 250 years of history unfold and is ready for its next chapter. Set on nearly 5 usable acres of level former farmland, the property features a spacious, updated interior along with multiple outbuildings and endless possibilities. Inside, you'll find over 3,000 sq. ft. of living space with 3 bedrooms, 2.5 baths, 2 fireplaces, and the warmth and character you expect from a home of this vintage. Outside, 2 barns await your vision, whether for hobbies, storage, animals, or something entirely new. And the opportunity doesn't stop there! Included is #51 across the street, a 1.09-acre parcel currently undergoing approvals as an additional building lot. The 3.72-acre home parcel at #50 is also undergoing approvals for a potential subdivision, creating the possibility of up to 3 lots for the price of one! Imagine a family compound, future development, or simply preserving the acreage and privacy for yourself. Located at the quiet intersection of Merwin Brook Road and Obtuse Road North, you'll feel tucked away in the country while remaining minutes from Brookfield amenities and conveniences, with numerous walking trails nearby, including just a 15-minute walk to lake Lillinonah! History, acreage, flexibility, and opportunity all in one remarkable offering!

50 Obtuse Rd N, Brookfield

$1,395,000
5 Beds 7 Baths ACTIVE Status 24200896 MLS
This is a must-see property to truly appreciate its remarkable scale, flexibility, and one-of-a-kind design. A perfect blend of historic charm and modern luxury, this residence seamlessly combines an original 1900 home with a thoughtfully designed 2004 expansion. Offering 5 bedrooms, 4 full and 3 half baths, the home showcases exceptional craftsmanship and distinctive architectural details throughout. A potential main-level in-law or au pair suite with a separate entrance, a versatile three-room space above the barn, and 7 garage bays provide exceptional functionality for multigenerational living, working from home, hobbies, or the avid car enthusiast. A grand foyer welcomes you into a dramatic family room anchored by a striking stone fireplace, flowing seamlessly into the living room and spacious kitchen. The kitchen features a center island, wine cooler, and Dacor stove/oven, while French doors open to a large deck that connects to a screened-in porch, extending the living space outdoors. The main level also features a stunning oak library, formal dining room, convenient mudroom entry, and walk-in pantry. A sun-filled conservatory surrounded by lush greenery offers a tranquil retreat and is equipped with automatic sprinklers, making it an ideal space for gardening enthusiasts.

109 Long Meadow Hill Rd, Brookfield

$799,000
4 Beds 4 Baths ACTIVE Status 24199516 MLS
Tucked into one of Brookfield's most coveted pockets, 28 Oak Grove Road sits on a leve lot where classic curb appeal meets modern comfort. A white picket fence welcomes you home, while out back, a private heated pool and screened porch overlooking the yard invite long summer afternoons. This 3,500+ sq ft classic Colonial unfolds with warmth and light - new hardwood floors flow across most of the main level, leading into a front-to-back living room. A renovated kitchen/dining area built for entertaining flows into the oversized family room which anchors the home with vaulted ceilings, walls of windows and a pellet stove. Retreat to one of 4 well-appointed bedrooms, including a spacious primary suite with a large walk-in closet and full bath. Downstairs, the lower level offers flexible bonus living space - full bath, ample living areas, a fireplace, private walk-out entrance, and its own patio with in law potential. Thoughtfully updated throughout: new roof and solar (2023), renovated kitchen (2024), two new electrical panels with upgraded service and generator hookup (2024), new water heater (2026), and fresh tile in the main-level half bath and entry. A Culligan water filtration system and two air purifiers serve the lower level, and the washer/dryer have been relocated to the main floor. Mature trees and seasonal plantings ring the yard for year-round privacy. Minutes to top Brookfield schools, Candlewood Lake, Lillinonah, I-84/Route 7

28 Oak Grove Rd, Brookfield

$749,900
4 Beds 3 Baths ACTIVE Status 24193965 MLS
Welcome home to this meticulously maintained, spacious Colonial offering 3,350 sq. ft. of light-filled living space plus incredible expansion potential in the oversized lower level. Step into a striking two-story foyer anchored by an elegant curved staircase. The main level features a large kitchen equipped with newer appliances, a private den and an inviting family room centered around a warm fireplace. Upstairs the primary suite features a versatile layout with an adjoining room perfect for a private home office, sitting room, or nursery. Outdoors enjoy an expansive deck built for effortless entertaining and family gatherings. Recent updates include a newer heating system and updated windows. This move-in-ready home is ideally situated just minutes from Candlewood Lake recreation, local amenities, and major highways.

1 Stony Farm Ln, Brookfield

$699,900
4 Beds 3 Baths ACTIVE Status 24191261 MLS
Welcome to this beautifully maintained Colonial, perfectly situated on 1.89 private acres in one of Brookfield's most desirable neighborhoods. Offering over three levels of thoughtfully designed living space, this 4-bedroom, 2.5-bath home combines classic New England character with the updates today's buyers are looking for. At the heart of the home is a spacious eat-in kitchen featuring abundant cabinetry, a pantry, and an easy flow into the dramatic family room with vaulted ceilings and a striking fireplace-an ideal space for both everyday living and entertaining. Formal living and dining rooms provide additional gathering spaces, while a dedicated home office offers the flexibility to work from home. Just beyond, the screened porch with skylights creates a peaceful retreat overlooking the private backyard. Upstairs, the spacious primary suite features an en-suite bath with a walk-in shower, accompanied by three additional generously sized bedrooms and a full hall bath. The finished lower level offers endless possibilities for a media room, fitness space, playroom, or guest retreat, along with exceptional storage. Step outside to enjoy the serenity of the beautifully wooded property- relax, unwind and take in the peaceful surroundings. Additional highlights include central air, a whole-house automatic generator, and numerous recent improvements, including a new roof (2024), septic tank (2023), furnace (2022), updated flooring, appliances & paint

7 Arapaho Rd, Brookfield

$695,000
4 Beds 3 Baths ACTIVE Status 24189998 MLS
Set on nearly an acre, this classic 4-bedroom, 2.5-bath colonial offers comfortable living space with an inviting private yard with stone walls and low maintenance plantings. A full flagstone front porch invites you to relax and take in spectacular sunset views, while two connected backyard flagstone patios create space to entertain and unwind. Inside, the sun-filled, eat-in kitchen overlooks the backyard with access to the two backyard patios. A comfortable dining room, bright living room and family room with fireplace offer flexibility for everyday living. The attached 2-car garage has easy entry to the kitchen and the full basement provides ample storage. Updates include a new septic system (June 2026), central air conditioning, and a portable generator with dedicated hookup. The house is situated on a quiet loop street with no through-traffic. Brookfield's highly rated schools, great parks, a golf course, a regional YMCA, abundant shopping, and I-84 are all just 5-minutes away. This home is both comfortable and convenient!

21 White Pine Dr, Brookfield

$748,000
3 Beds 3 Baths ACTIVE Status 24188079 MLS
Nestled on a quiet cul-de-sac in the desirable Carriage Homes on The Pond community, this detached condominium offers 3 bedrooms, 2.5 baths, and a flexible floor plan. The main level features vaulted ceilings, gas fireplace, and three sliders to a Trex-style deck overlooking expansive lawns. The first-floor primary suite includes a large walk-in closet and en-suite bath with tub and separate shower. Eat-in kitchen with granite countertops, center island, and pantry. Main level also offers a private office with French doors, half bath, laundry, and attached garage. Upstairs features two spacious bedrooms, full bath, and loft area. Full basement provides excellent storage and future finishing potential. Enjoy single-family privacy with low-maintenance condo living in one of Brookfield's most sought-after communities.

6 Carriage House Ln Unit 6, Brookfield

$700,000
4 Beds 3 Baths ACTIVE Status 24187557 MLS
Nestled on a private, beautifully landscaped lot in the highly sought-after Barkwood Falls community that includes beach rights, canoe/kayak storage and boat dock, this charming four-bedroom, two full and one-half bath Colonial offers the perfect blend of comfort, style, and lake community living. The inviting main level features a spacious eat-in kitchen with granite countertops and tile flooring, formal living and dining room, a cozy family room with a fireplace, and a sun-filled sunroom with pellet stove and vaulted ceilings that brings the outdoors in. Upstairs, you'll find a spacious primary suite along with three additional bedrooms, providing plenty of room for family and guests. Outside, the grounds have been lovingly cultivated using many native species, creating a spectacular perennial display of color and texture throughout the seasons. Additional storage space located in the shed under the sunroom. Just steps from your door, enjoy Barkwood Falls' private sandy beach, picnic area, playground, and boat launch. Dock slips are available by waitlist for just $25 per foot, while kayak or canoe storage is only $175 per space annually. The low annual association dues of just $200 makes it easy to enjoy all the amenities this wonderful lake community has to offer. Conveniently located close to shopping, downtown, and major highways, this exceptional home offers the perfect balance of privacy, convenience, and year-round recreation.

3 Deerfield Rd, Brookfield

$799,000
6 Beds 4 Baths ACTIVE Status 24172351 MLS
Located in sought-after Greenknoll Drive located in the heart of Brookfield, this spacious Colonial offers a rare and flexible floor plan with six bedrooms and four full baths, connected to PUBLIC SEWER. A main-level bedroom and full bath provide the ideal setup for guests, multigenerational living, or a home office. Upstairs you'll find four additional bedrooms, while the lower level features a sixth bedroom creating excellent potential for an in-law or guest suite with full bath and direct access to its own private deck. This home has been thoughtfully updated throughout. The kitchen was totally remodeled in Fall of 2025, and all bathrooms have been tastefully renovated as well. New laminate flooring has replaced the majority of the carpeted areas beautifully complementing the exsisting hardwood floors creating a cohesive, move-in ready interior. Combinding generous living space, modern updates, and highly desirable Brookfield location, this home is a rare opportunity not to be missed.

33 Greenknoll Dr, Brookfield

$762,000
4 Beds 4 Baths ACTIVE Status 24183828 MLS
The perfect balance of elegance, comfort, and modern living awaits you in this beautiful Colonial located in this highly sought after Lillinonah area neighborhood that has deeded lake rights! Nestled on over 2 private acres at the end of a quiet cul-de-sac. This exceptional home offers space, character, and value at every turn. The main level features an open -concept floor plan with an eat-in kitchen, formal dining room, spacious living room, powder room and a convenient laundry room complete with brand new washer and dryer. Custom trim work throughout the main floor adds warmth and satisfaction while the stunning new front door creates an inviting first impression. A mudroom provides direct access to the garage, and the kitchen opens up to an expansive deck through both a sliding glass door and an additional exterior door perfect for indoor-outdoor entertaining. Upstairs, you'll find four generously sized bedrooms and two full bathrooms, including a spacious primary suite featuring a vaulted ceiling, modern en-suite bath and walk-in closet. The fully finished walkout basement offers incredible flexibility with a full bathroom, two large finished spaces ideal for a home office, gym, playroom, media room, homeschooling area or guest accommodations. Step outside to the patio and enjoy the expansive backyard surrounded by privacy and nature. Whether you're seeking room to grow, space to work from home or a property designed for entertaining this home truly has it all.

4 Fleetwood Ln, Brookfield

$730,000
3 Beds 3 Baths ACTIVE Status 24183592 MLS
Welcome to this beautifully updated colonial, featuring key improvements throughout including updated kitchen and bathrooms, a new roof, new AC, and freshly painted interior and exterior. The front porch provides a relaxing space that leads into the welcoming foyer with a center hall staircase and plentiful closet space. To your left is the front to back living room nicely decorated with a focal point on the fireplace and beautiful bay window overlooking the private front yard. Into the open kitchen you will find great space for everyday cooking and activities or hosting larger gatherings or holidays. Step down from the kitchen into the family room/playroom with built in shelving and bookcases - a great space to read or play games. Sliders out to a new deck provide smooth indoor-outdoor flow. Downstairs is an additional room that can be used for movies, music rehearsals, gym equipment or just added space as needed. There is yet another room in the lower level, currently set up as a guest room but is perfect as a home office or 4th bedroom. Upstairs the primary bedroom has an amazing en suite bathroom with a walk-in shower and separate soaking tub with double sinks and lots of natural light. Two other good-sized bedrooms share another updated bathroom with walk in shower, soaking tub and double vanity. A smaller bonus room, currently used as a nursery, offers great flexibility as a storage closet, homework nook, or giftwrapping room! So much to see and awesome location!!

8 White Pine Dr, Brookfield

$1,295,000
4 Beds 4 Baths ACTIVE Status 24173739 MLS
REDUCED to SELL! Quintessential Vintage Farmhouse, circa 1784, on 2.31 glorious, manicured acs, adorned w/perennial gardens that signal the seasons. Offering the best of today's modern amenities with the charm of yesteryear, this 4 BR, 4.5 bath Colonial Farmhouse w/3 bay barn garage, is the ultimate for the antique lover. The main entry, showcases a formal living room w/fireplace, adjacent dining room with bay window plus a den with fireplace serving as an ideal TV room or reading room. The rear of the house forms the focal point with/its covered Mahogany porch, wrap deck & stone terrace w/stone fireplace viewing the pool & gardens. A vaulted primary suite hosts balcony, private bath, huge WIC w/built-ins & a TV room. New Chef's kitchen w/high end appliances, 3 working fireplaces, new wide board honed floors in great room & kitchen, granite counters, serving bar, coffee bar & more; ideal for the entertainer. The in ground gunite pool, surrounded by perennial gardens & cast aluminum fencing is set apart but easily viewed from the main house. A 3 bay barn garage is enhanced with a loft housing a gym, full bath and extra guest room, possibly an optional in-law suite. A true gem of the past, restored lovingly through generations, the provenance carefully protected from family to family.Other upgrades incl:new roof (2025), new windows , new hot water heater (2023),new well pump & tank( 2026), whole house generator, updated baths, wood stove in family room, new vinyl fencing+

49 Old Bridge Rd, Brookfield

$1,195,000
4 Beds 4 Baths ACTIVE Status 24178021 MLS
Welcome to 4 D'Arcangelo Drive, a meticulously crafted Colonial set on over two acres at the end of a quiet cul-de-sac in Brookfield. Built in 2022 with exceptional attention to detail, this 4-bedroom, 3.5 bathroom home offers 4,524 square feet of thoughtfully designed living space that still feels practically new. Nine-foot ceilings, custom millwork, and hardwood flooring flow throughout the main level. The eat-in kitchen features custom white cabinetry, quartz countertops, a generous center island, stainless steel appliances, and a walk-in pantry. An open floor plan connects to a spacious family room with fireplace, formal dining room, and a main-level library with French doors, a first floor built equally for everyday living and gracious entertaining. Upstairs, four bedrooms and three full baths include a primary suite spanning over 1,000 square feet with a sitting area, dedicated dressing room, oversized custom-tiled shower, and soaking tub. A three-car attached garage, central air, and a full basement with future finishing potential complete the package. Brookfield offers the Still River Greenway for hiking and biking, and proximity to Candlewood Lake for boating, fishing, and waterfront dining, all minutes from Federal Road and I-84 for an easy commute to Danbury, Stamford, and New York City.

4 Darcangelo Dr, Brookfield

$2,249,000
3 Beds 4 Baths ACTIVE Status 24172376 MLS
Stunning newly built lakefront residence offering over 3284sqf of thoughtfully designed living space. Ideal fits for own resident or Airbnb.This home features 3 spacious bedrooms, including an extra-large flex room ideal as a 4th bedroom or home office, three full bathrooms, and one half bath.The primary suite is a private retreat with a walk-in closet and separate access to the deck through aluminum sliding door, perfect for enjoying morning coffee with breathtaking lake views. The spa-like primary bathroom features a freestanding soaking tub, oversized shower with elegant gold fixtures, double vanity, heated floors, and tall aluminum windows that flood the space with natural light. Two additional bedrooms offer generous closet space and share a beautifully appointed guest bathroom. The main level boasts a spacious dining area leading into a chef's kitchen equipped with Viking appliances, custom inset cabinetry, white oak island and cabinetry, and a striking coffered ceiling, all overlooking the lake. The kitchen seamlessly connects to the living and family rooms, highlighted by big aluminum sliding door and a custom white oak wall unit with built-in TV. The lower level offers exceptional flexibility with a large playroom and an additional family lounge, both featuring oversized aluminum sliding doors and abundant natural light and access to the patio. Exceptional lake lifestyle opportunity.

20 N Lake Shore Dr, Brookfield

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