Jennifer Kelley's profile photo

Jennifer Kelley

Licensed Real Estate Salesperson
jennifer.kelley@compass.com
M: 203-948-2864
About Jennifer
Jennifer Kelley is a Principal at The Encore Team at Compass, a powerhouse, partner-led collective built on the legacy and success of Around Town Real Estate. With a strong foundation in market performance, hyper-local expertise, and a collaborative approach, the team delivers a level of strategy, creativity, and execution rarely found in traditional real estate.

Guided by her signature philosophy, “Moving you forward, with heart,” Jennifer brings a refined yet deeply personal approach to every client experience. She understands that home is more than a transaction — it’s a meaningful life transition — and she is known for navigating each step with intention, clarity, and care.

A lifelong Fairfield County resident and 25+ year Newtown local, Jennifer offers clients an insider’s perspective on the community she proudly calls home. She and her husband, Patrick, have chosen to raise their children, Reagan and Declan, in the very town that shaped their own lives — a connection that informs both her work and her commitment to her clients.

Prior to real estate, Jennifer built a successful career in finance, equipping her with the analytical expertise and strategic mindset needed to guide clients through complex decisions with confidence. Today, she seamlessly blends that business acumen with a relationship-first approach, ensuring each client feels supported, informed, and empowered.

For those seeking a thoughtful, elevated real estate experience backed by proven results and genuine care, Jennifer delivers — every time.

Jennifer Kelley’s Listings

a view of a white house with a large yard and large tree
a view of a terrace with a lake view
a view of gallery with wooden floor
a view of a big room with wooden floor and windows
a view of an empty room with wooden floor
a view of an empty room with a window and fireplace
a view of an empty room with wooden floor and cabinet
a living room with a fireplace and wooden floor
a view of an empty room with a window and wooden floor
a living room with furniture and a large window
a view interior of the house
a living room with furniture and a table
a view of an empty room with wooden floor and a window
a bathroom with a sink and a mirror
a view of living room kitchen with stove and wooden floor
a view of a dining room with furniture window and wooden floor
a kitchen with granite countertop kitchen island stainless steel appliances a sink and wooden cabinets
a kitchen with stainless steel appliances granite countertop a stove a sink and a refrigerator
a kitchen with a sink and a stove
a kitchen with granite countertop a stove a sink and a refrigerator
a big room with wooden floor and closet area
a living room with furniture and a flat screen tv
a bathroom with a granite countertop sink and a mirror
a bathroom with a granite countertop shower and a sink
a view of a livingroom with wooden floor
wooden floor in an empty room with a window
a bedroom with a bed and a flat screen tv
a view of an empty room with wooden floor and a window
a view of an empty room with wooden floor and closet
a view of an empty room with window and wooden floor
a view of empty room
a view of empty room with wooden floor and fan
a bathroom with a sink toilet a mirror and shower
a view of a livingroom with wooden floor and a window
a view of a city from a balcony
a white house that has a tree in front of it
a view of a house with a yard and garage
a view of a house with a yard
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
1/40
Listed By CompassUnder Contract - Continue To Show

$684,000

4
Bedrooms
2,874
Square Feet
4.7
Acres

74 Middle Quarter Road, Woodbury, CT 06798

a front view of a house with a yard and trees
a house view with a garden space
a view of entryway and hall with wooden floor
a living room with furniture and a wooden floor
a living room with furniture fireplace and flat screen tv
a living room with furniture fireplace and flat screen tv
a living room with furniture flat screen tv and a fireplace
a living room with stainless steel appliances furniture and a kitchen view
a dining room with furniture a kitchen view and a chandelier
a living room with stainless steel appliances furniture and a kitchen view
a dining room with furniture a chandelier and wooden floor
a kitchen with a refrigerator sink and microwave
a kitchen with granite countertop a sink stove and cabinets
a view of a dining room with furniture window and outside view
a bedroom with a bed and wooden floor
a bedroom with a bed and a dresser
a bedroom with a bed and a television
a bathroom with a sink and a mirror
a bedroom with a bed and flat screen tv
a bathroom with a sink toilet and shower
a bathroom with a toilet and shower curtain
a room with furniture and a fireplace
a room with furniture a flat screen tv and a stool
a view of a hallway with paintings on the wall
a bedroom with furniture and a window
a room with storage and utility
a living room with furniture a flat screen tv and a table
a bedroom with furniture and stairs
a bathroom with a sink mirror and toilet
a bathroom with a sink a toilet and a mirror
a view of a room with gym equipment
a view of a roof deck with table and chairs and a fire pit
a view of a patio with couches chairs and wooden floor
a view of a house with a backyard and sitting area
a view of a terrace
a view of a terrace with furniture
an aerial view of residential houses with outdoor space and trees
$510,000 | 16 Curtis Avenue, New Fairfield, CT 06812
$510,000 | 16 Curtis Avenue, New Fairfield, CT 06812
$510,000 | 16 Curtis Avenue, New Fairfield, CT 06812
1/40
Listed By CompassUnder Contract - Continue To Show

$510,000

3
Bedrooms
1,414
Square Feet
0.25
Acres

16 Curtis Avenue, New Fairfield, CT 06812

Jennifer Kelley’s Transactions

Past Sales
a front view of a house with garden

$1,614,357

5
Bedrooms
7,919
Square Feet
2.05
Acres

5 Vona Way, Newtown, CT 06470

a front view of a house with a yard

$1,450,000

5
Bedrooms
6,000
Square Feet
2.05
Acres

5 Vona Way, Newtown, CT 06470

a front view of a house with a yard

$1,225,000

6
Bedrooms
6,074
Square Feet
1.95
Acres

13 Sugar Street, Newtown, CT 06470

a front view of a house with garden

$1,100,000

3
Bedrooms
2,700
Square Feet

104 Stillson Road, Unit 104, Fairfield, CT 06825

$1,060,000 | 130 Branch Brook Road, Wilton, CT 06897

$1,060,000

5
Bedrooms
6,607
Square Feet
2
Acres

130 Branch Brook Road, Wilton, CT 06897

a view of a house with a yard table and chairs

$1,050,000

5
Bedrooms
4,146
Square Feet
4.55
Acres

9 Farmery Lane, Newtown, CT 06482

$1,000,000 | 8 Boulder Creek Road, Newtown, CT 06470

$1,000,000

5
Bedrooms
6,116
Square Feet
2.09
Acres

8 Boulder Creek Road, Newtown, CT 06470

an aerial view of a house with swimming pool a yard and lake view

$950,000

4
Bedrooms
2,363
Square Feet
0.6
Acres

53 Bogus Hill Road, New Fairfield, CT 06812

a front view of house with yard and green space

$950,000

4
Bedrooms
4,006
Square Feet
2.02
Acres

50 Marlin Road, Newtown, CT 06482

$935,000 | 12 Plumb Creek Road, Trumbull, CT 06611

$935,000

4
Bedrooms
3,899
Square Feet
1
Acres

12 Plumb Creek Road, Trumbull, CT 06611

a front view of a house with a garden and trees

$925,000

4
Bedrooms
3,388
Square Feet
0.6
Acres

310 Fairland Drive, Fairfield, CT 06825

a front view of a house with swimming pool and porch

$850,000

4
Bedrooms
3,363
Square Feet
2.02
Acres

3 Quarry Ridge Road, Newtown, CT 06482

$832,000 | 11 Ashwood Lane, Brookfield, CT 06804

$832,000

4
Bedrooms
3,925
Square Feet
1.97
Acres

11 Ashwood Lane, Brookfield, CT 06804

a front view of a building with trees around

$825,000

3
Bedrooms
3,496
Square Feet
1.03
Acres

10 Pinnacle Drive, Newtown, CT 06470

$825,000 | 27 Yogananda Street, Newtown, CT 06482

$825,000

4
Bedrooms
3,713
Square Feet
2.7
Acres

27 Yogananda Street, Newtown, CT 06482

$822,000 | 2 Old Farm Hill Road, Newtown, CT 06470

$822,000

5
Bedrooms
3,471
Square Feet
2.3
Acres

2 Old Farm Hill Road, Newtown, CT 06470

$820,000 | 210 Brushy Hill Road, Newtown, CT 06470

$820,000

4
Bedrooms
3,300
Square Feet
2.01
Acres

210 Brushy Hill Road, Newtown, CT 06470

front view of a house with a yard

$806,000

4
Bedrooms
3,044
Square Feet
1.34
Acres

10 Hanover Road, Newtown, CT 06470

Past Rentals
$2,900 | 9 Harmony Lane, Monroe, CT 06468

$2,900

3
Bedrooms
2,388
Square Feet
1.1
Acres

9 Harmony Lane, Monroe, CT 06468

a living room with furniture a fireplace and a flat screen tv

$2,000

1
Bedrooms
1,200
Square Feet
1.33
Acres

4 Lands End Road, Newtown, CT 06470

$2,000 | 40 Cliff Street, Shelton, CT 06484

$2,000

3
Bedrooms
1,219
Square Feet
0.15
Acres

40 Cliff Street, Shelton, CT 06484

$1,750 | 85 Chestnut Street, Unit G, Bethel, CT 06801

$1,750

1
Bedrooms
764
Square Feet

85 Chestnut Street, Unit G, Bethel, CT 06801

a front view of a house with a yard

$1,400

1
Bedrooms
859
Square Feet
0.15
Acres

40 Cliff Street, Shelton, CT 06484